微溶剂中通过硼氢化钠还原吡咯醛来制备新颖吡咯醇
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摘要
以β酮酸酯为起始原料,经亚硝化、Knorr缩合和硝酸铈铵氧化后得到了10个吡咯醛,然后在微量的聚乙二醇中,于室温下研磨硼氢化钠和吡咯醛,使其呈现面团状态,然后经放置反应而获得10个吡咯醇.全部化合物结构均通过IR、1H-NMR和ESI MS表征,其结果和目标化合物一致.在微溶剂中,用硼氢化钠还原吡咯醛来制备吡咯醇,该法具有操作简单、能耗低、合成效率高以及环境友好等优点.其中,5个吡咯醛(2c,2f,2h-2j)和8个吡咯醇(3a-3d,3f,3h-3j)是首次报道的新化合物.
In the report,ten pyrrole aldehydes were prepared from β-keto acid esters by nitrosation,Knorr condensation and oxidation with ammonium ceric nitrate. Then,in the medium of micro PEG-600,the pyrrole aldehydes and sodium borohydride were grinded into the shape of dough using an agate mortar and pestle and then kept at room temperature. The corresponding alcohols were obtained. All the compounds were characterized and determined by IR,1H NMR,and ESI MS. Among them,5 pyrrole aldehydes( 2c,2f,2h ～ 2j) and 8 pyrrole alcohols( 3a ～ 3d,3f,3h ～ 3j) are new compounds. This synthesis method for the reduction of pyrrole aldehydes with NaBH4 has the advantage of simple operation,low energy consumption,high yield and environmental friendly.
In the report,ten pyrrole aldehydes were prepared from β-keto acid esters by nitrosation,Knorr condensation and oxidation with ammonium ceric nitrate. Then,in the medium of micro PEG-600,the pyrrole aldehydes and sodium borohydride were grinded into the shape of dough using an agate mortar and pestle and then kept at room temperature. The corresponding alcohols were obtained. All the compounds were characterized and determined by IR,1H NMR,and ESI MS. Among them,5 pyrrole aldehydes( 2c,2f,2h ～ 2j) and 8 pyrrole alcohols( 3a ～ 3d,3f,3h ～ 3j) are new compounds. This synthesis method for the reduction of pyrrole aldehydes with NaBH4 has the advantage of simple operation,low energy consumption,high yield and environmental friendly.
引文
[1]Aghapoor K,Mohsenzadeh F,Darabi H R,et al. 1-tryptophan-catalyzed paal-knorr pyrrole cyclocondensation:an efficient,clean and recyclable organocatalyst[J]. Research on Chemical Intermediates,2016,42(2):407-415.
[2]Pillonel C,Meyer T. Effect of phenylpyrroles on glycerol accumulation and protein kinase activity of Neurospora crassa[J].Pest Management Science,2015,49(3):229-236.
[3]Keyzers R A,Arendse C E,Hendricks D T,et al. Makaluvic acids from the south sfrican latrunculid sponge Strongylodesma aliwaliensis[J]. Journal of Natural Products,2005,68(4):506-510.
[4]Zhou H,Xie Y,Baloch Z,et al. The effect of atorvastatin,3-hydroxy-3-methylglutaryl coenzyme a reductase inhibitor(HMG-Co A),on the prevention of osteoporosis in ovariectomized rabbits[J]. Journal of Bone&Mineral Metabolism,2016:1-10.
[5]Yilmaz O,Karagol I H E,Topal E,et al. Tolmetin:An option for multiple NSAID hypersensitivity in a preschooler[J]. Pediatric Allergy Immunology&Pulmonology,2013,26(3):164-165.
[6]Cocco D,Giancaspro C,Monaci A,et al. A study of the alkylation of methylbenzenes[J]. Cheminform,1983,14(22):5217-5220.
[7]郁惠蕾,黄磊,倪燕,等.羰基生物还原法合成手性醇的研究进展[J].生物加工过程,2013,11(3):71-82.
[8]Micheli F,Di F R,Bordi F,et al. 2,4-dicarboxy-pyrroles as selective non-competitive m GluR1 antagonists:further characterization of 3,5-dimethyl pyrrole-2,4-dicarboxylic acid 2-propyl ester 4-(1,2,2-trimethyl-propyl)ester and structure-activity relationships[J]. Bioorganic&Medicinal Chemistry Letters,2003,13(13):2113-2118.
[9]Fu Y,Wang J Y,Zhang D,et al. Solvent-free synthesis and safener activity of sulfonylurea benzothiazolines[J]. Molecules,2017,22(10):1601-1610.
[10]Toda F,Kiyoshige K,Yagi M. Na BH4reduction of ketones in the solid state[J]. Angewandte Chemie-International Edition,1989,28:320-321.
[11]Marchand A P,Reddy G M. Stereospecific solid state sodium borohydride reductions of cage dikotenes[J]. Cheminform,1991,22(48):6571-6576..
[12]Varma R S,Saini R K. Microwave-assisted reduction of carbonyl compounds in solid state using sodium borohydride supported on alumina[J]. Tetrahedron Letters,1997,38:4337-4338.
[13]Perin G,Barcellos A M,Luz E Q,et al. Green hydroselenation of aryl alkynes:divinyl selenides as a precursor of resveratrol[J]. Molecules,2017,22(2):327-338.
[14]Nakane S,Yoshinaka S,Iwase S,et al. Synthesis of fluspidine via asymmetric Na BH4reduction of silicon enolates ofβ-keto esters[J]. Tetrahedron,2018,74(38):5069-5084.
[15]Liu X,Ren L. The influence of polyethylene glycol on the synthesis and activity of MoP for the hydrodechlorination of trichloroethylene[J]. Rsc Advances,2016,6(9):7413-7418.
[16]Li L,Shang L,Chen K,et al. Redox-sensitive core cross-linked polyethylene glycol-polypeptide hybrid micelles for anticancer drug delivery[J]. Journal of Nanoscience&Nanotechnology,2017,17(7):4532-4541.
[17]Dhayadhul A,Kumar R S,Nasser A J A,et al. Synthesis of some pyrrole derivatives and their anticoagulant activity[J]. American Journal of Drug Discovery&Development,2012,2(1):40-49.
[18]Bell I M,Stirdivant S M,Ahern J,et al. Biochemical and structural characterization of a novel class of inhibitors of the type1 insulin-like growth factor and insulin receptor kinases[J]. Biochemistry,2005,44(27):9430-9440.
[19]赵婕妤.查尔酮衍生物的合成及其杀螨活性[D].杨凌:西北农林科技大学,2016.
[20]Schendorf T M,Del Vecchio R,Koech K,et al. A standard protocol for Na BH4reduction of CDOM and HS[J]. Limnology&Oceanography Methods,2016,14(6):414-423.
[21]Zeynizadeh B,Behyar T. Fast and efficient method for reduction of carbonyl compounds with Na BH4/Wet Si O2under solvent free condition[J]. Journal of the brazilian chemical Society,2005,16:1200-1209.
[22]Naimi-Jamal M R,Reza,Mokhtari J,et al. Sodium tetraalkoxyborates:intermediates for the quantitative reduction of aldehydes and ketones to alcohols through ball milling with Na BH4[J]. European Journal of Organic Chemistry,2009,44:3567-3572.
[2]Pillonel C,Meyer T. Effect of phenylpyrroles on glycerol accumulation and protein kinase activity of Neurospora crassa[J].Pest Management Science,2015,49(3):229-236.
[3]Keyzers R A,Arendse C E,Hendricks D T,et al. Makaluvic acids from the south sfrican latrunculid sponge Strongylodesma aliwaliensis[J]. Journal of Natural Products,2005,68(4):506-510.
[4]Zhou H,Xie Y,Baloch Z,et al. The effect of atorvastatin,3-hydroxy-3-methylglutaryl coenzyme a reductase inhibitor(HMG-Co A),on the prevention of osteoporosis in ovariectomized rabbits[J]. Journal of Bone&Mineral Metabolism,2016:1-10.
[5]Yilmaz O,Karagol I H E,Topal E,et al. Tolmetin:An option for multiple NSAID hypersensitivity in a preschooler[J]. Pediatric Allergy Immunology&Pulmonology,2013,26(3):164-165.
[6]Cocco D,Giancaspro C,Monaci A,et al. A study of the alkylation of methylbenzenes[J]. Cheminform,1983,14(22):5217-5220.
[7]郁惠蕾,黄磊,倪燕,等.羰基生物还原法合成手性醇的研究进展[J].生物加工过程,2013,11(3):71-82.
[8]Micheli F,Di F R,Bordi F,et al. 2,4-dicarboxy-pyrroles as selective non-competitive m GluR1 antagonists:further characterization of 3,5-dimethyl pyrrole-2,4-dicarboxylic acid 2-propyl ester 4-(1,2,2-trimethyl-propyl)ester and structure-activity relationships[J]. Bioorganic&Medicinal Chemistry Letters,2003,13(13):2113-2118.
[9]Fu Y,Wang J Y,Zhang D,et al. Solvent-free synthesis and safener activity of sulfonylurea benzothiazolines[J]. Molecules,2017,22(10):1601-1610.
[10]Toda F,Kiyoshige K,Yagi M. Na BH4reduction of ketones in the solid state[J]. Angewandte Chemie-International Edition,1989,28:320-321.
[11]Marchand A P,Reddy G M. Stereospecific solid state sodium borohydride reductions of cage dikotenes[J]. Cheminform,1991,22(48):6571-6576..
[12]Varma R S,Saini R K. Microwave-assisted reduction of carbonyl compounds in solid state using sodium borohydride supported on alumina[J]. Tetrahedron Letters,1997,38:4337-4338.
[13]Perin G,Barcellos A M,Luz E Q,et al. Green hydroselenation of aryl alkynes:divinyl selenides as a precursor of resveratrol[J]. Molecules,2017,22(2):327-338.
[14]Nakane S,Yoshinaka S,Iwase S,et al. Synthesis of fluspidine via asymmetric Na BH4reduction of silicon enolates ofβ-keto esters[J]. Tetrahedron,2018,74(38):5069-5084.
[15]Liu X,Ren L. The influence of polyethylene glycol on the synthesis and activity of MoP for the hydrodechlorination of trichloroethylene[J]. Rsc Advances,2016,6(9):7413-7418.
[16]Li L,Shang L,Chen K,et al. Redox-sensitive core cross-linked polyethylene glycol-polypeptide hybrid micelles for anticancer drug delivery[J]. Journal of Nanoscience&Nanotechnology,2017,17(7):4532-4541.
[17]Dhayadhul A,Kumar R S,Nasser A J A,et al. Synthesis of some pyrrole derivatives and their anticoagulant activity[J]. American Journal of Drug Discovery&Development,2012,2(1):40-49.
[18]Bell I M,Stirdivant S M,Ahern J,et al. Biochemical and structural characterization of a novel class of inhibitors of the type1 insulin-like growth factor and insulin receptor kinases[J]. Biochemistry,2005,44(27):9430-9440.
[19]赵婕妤.查尔酮衍生物的合成及其杀螨活性[D].杨凌:西北农林科技大学,2016.
[20]Schendorf T M,Del Vecchio R,Koech K,et al. A standard protocol for Na BH4reduction of CDOM and HS[J]. Limnology&Oceanography Methods,2016,14(6):414-423.
[21]Zeynizadeh B,Behyar T. Fast and efficient method for reduction of carbonyl compounds with Na BH4/Wet Si O2under solvent free condition[J]. Journal of the brazilian chemical Society,2005,16:1200-1209.
[22]Naimi-Jamal M R,Reza,Mokhtari J,et al. Sodium tetraalkoxyborates:intermediates for the quantitative reduction of aldehydes and ketones to alcohols through ball milling with Na BH4[J]. European Journal of Organic Chemistry,2009,44:3567-3572.